HCID 44580262, compound → HCID 59793630, compound

HRID 736164Notes

Reaction equation

HRID 736164 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:17])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[C:8]([C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)=[O:17])[CH:9]=1

Participants

5

Reactant 2

HCID 44580262HCID 44580262, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59793630HCID 59793630, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-Morpholin-4-yl-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (preparation described in example 57, 150 mg, 0.323 mmol) in methanol (3 ml) was added Pd/C 10% (6.9 mg). The mixture was stirred under an atmospheric pressure of hydrogen at room temperature for 1 hour. Catalyst was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed over silicagel (Eluent: Heptane/Ethylacetate (0-100% in 20 minutes)) to provide the title compound (111 mg, 79% yield) as a yellow solid, MS (m/e): 435.2 (M+H+, 100%).

Workup

  1. filtrationCatalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed over silicagel (Eluent: Heptane/Ethylacetate (0-100% in 20 minutes))

Sources & evidence

ORD record
ord-d6c070b1d1c846069dfae0b7a9742797
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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